STAY. 

  • Crow’s Nest – The Montauk inn comes from the owner of NYC’s The Bowery Hotel and The Jane. It’s laid back vibe reflects Montauk charm. Just steps away from Ditch Plains beach, the guest rooms boast private decks overlooking Lake Montauk. When traveling with a group, the Cottages are a great option that allow you to entertain.

  • Sunset Beach – Shelter Island’s chic beach house. The restaurant and bar boasts a young summer crowd with a euro vibe. The guestrooms are minimalistic with pops of fun colors – each with their own private sundeck. Located directly across the Shelter Island Sound, the 20-room boutique hotel isthe perfect seaside escape.

  • The Maidstone Hotel – A recently reimagined East Hampton classic. The exterior is very familiar, that of a white Hampton’s colonial, while the interior now boasts a vibrant aesthetic and décor inspired by the Swedish owners. There’s also a new Chef in town, David Standridge of West Village’s Café Clover, who has taken over The Living Room restaurant with seasonal fresh menu items. Yoga in the garden and hotel bikes are also available for guests.

  • Topping Rose House – The Hamptons’ luxury establishment located in Bridgehampton. Think of an old refurbished white picket fence home with modern interiors, that’s Topping Rose. There ‘s also a Jean Georges restaurant inside so you know the food will be great too.

  • The Inn at Windmill Lane – A high end bed + breakfast located just a couple minutes from the village of Amagansett. The suites are beautiful with large soaking tubs perfect for peaceful getaway. There’s no bar or restaurant on site, but they have everything you need for the beach.

SNACK.

  • Sunset Beach - Seaside dining in Shelter Island serving a menu of Mediterranean favorites. A fun French Riviera vibe.

  • Suki Zuki – Casual Japanese located in Watermill. Must order: Teriyaki chicken salad.

  • The Clam Bar – A summer staple located on the side of Montauk highway.

  • Round Swamp Farm – Best gourmet farmers market in Bridge and East.

  • Lunches Lobster Roll – Montauk’s famous lobster spot.

  • Princess Diner + Candy Kitchen - Diners serving food that’s actually good.

  • EMP Summer House – The summer version of famed Eleven Madison Park. Upscale and fancy.

  • La Fondita – The Tacombi of Montauk serving Mexican.

  • Le Charlot – From the UES to Southampton, serving Classic French.

  • San Ambroeus – A Southampton staple with the best pasta and gelato. Ask for the outdoor seating in their Alleyway.

  • Highway – A cute, cozy yet modern eatery in East Hampton. From the people behind, Charlie Bird, Pasquale Jones, EMP and the Nomad.

  • Bostwicks - Favorite casual seafood spot in East Hampton. Outdoor seating and catering available.

  • Wolffer Kitchen – Casual neighborhood resto in Amagansett and Sag Harbor serving fresh food influenced by their wines.

  • Service Station – A roadside bar and grill serving American comfort food on Montauk Highway.

  • Vine Street Café – Shelter Island eatery with outdoor dining, a food truck and market place.

  • Lulu Kitchen + Bar – Serving wood-fired favorites in Sag Harbor.

  • Duryea’s Lobster Deck - Montauk’s upscale lobster joint the water.

  • Nick + Toni's - An iconic East Hampton eatery serving summertime Mediterranean/Italian. for over 25 years.

  • Sip'n Soda - The old fashioned family-run luncheonette and soda shop in the village of Southampton.

  • The Fudge Company - Ice cream, fudge and candy spot in South.

  • Scoop du Jour - Ice cream and frozen yogurt in East Hampton.

SIP.

  • Navy Beach - Montauk's casual seaside restaurant and bar.

  • The Surf Lodge - Perched on the edge of Lake Montauk, The Surf Lodge brings a boho chic vibe with a sought after summer concert series.

  • Ruschmeyer's - Another popular Montauk spot with a casual camp vibe.

  • Gurney's Montauk Resort + Seawater Spa - Recently renovated, Gurney's as revamped their look and the beverage program. The Beach Club is the perfect daytime destination for cocktails on the beach.

  • Sunset Beach - Always a great spot on Shelter Island to hang after lunch. They have a lounge area in the back with ping pong, ice cream and bocce.

  • Wolffer Estate Vineyard Wine Stand - The Wine Stand is an extension of Wolffer Estate, where people can enjoy live music, a bottle of wine and beautiful views of the vineyard on Saturdays and Sundays.

SEE + DO. 

  • Wolffer Estate Vineyard - Located in Sagaponack, this vineyard has become a Hampton favorite for wine tastings, tours and their latest restaurants.

  • Parris Art Museum - The Herzog and de Meuron-designed art center is a cultural destination in Water Mill with inspirational art exhibitions and programs.

  • Madoo Conservancy - Beautiful gardens in the center of Sagaponack, that hosts tours, lectures, events, workshops and children activities.

  • Southampton Carnival - An annual pop-up carnival that comes to Southampton every Summer. Ride, games, and carnival snacks. Days and hours change year to year.

  • Hank's Farm - Go-to for strawberry picking in the summertime and pumpkin picking in the fall.

SHOP.